When employees lack self-confidence, it can be hard to get them to perform at their best. So how can you help them excel at their job? What kind of coaching should you provide? What’s the best way to boost their self-esteem? And how do you deal with your own frustration around their Insecure behavior?

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What the Experts SayInsecure employees are “hard to evaluate, hard to coach, and hard to develop,” says Ethan Burris, an associate professor at the McCombs School of Business at the University of Texas, Austin. “The challenge is that insecure people are so concerned with how they look and how they are perceived that they either fail to solicit critical feedback or completely ignore it when it’s given. And this robs them of the opportunity to improve.” Your interpersonal relationships with insecure employees also tend to be more complicated, says Mary Shapiro, a professor at Simmons College School of Management and the author of HBR Guide to Leading Teams. As the boss, “you need to help them build confidence in their own capacity and help them change how they see themselves,” she says. It’s not an easy process. But with time and patience, you may begin to see a shift in the right direction. Here are a few strategies to try.

Reflect“Before you label your employee ‘insecure,’ ask yourself, ‘What evidence am I basing this on?’” says Shapiro. Is it because the person uses tentative language? Is it because she’s overly deferential to you? Is it because he’s always asking for reassurance? “Be careful in your interpretation.” It could be that what you perceive as insecurity is actually a “personality quirk,” a “cultural or social difference” or “a risk-averse” nature. Think, too, about why your perception of your employee’s insecurity is a problem, says Burris. Is your employee’s insecurity having a negative impact on team performance? Is it hurting morale? Or is it detrimental to that individual’s career? “You need to understand what you’re trying to solve before you go in with solutions,” Burris adds.

Be honest with your employeeWhile most managers are not equipped “to be armchair psychologists” and delve into “the underlying causes of their employees’ insecurities all the way back to their childhoods” they do have an obligation to tackle certain behaviors if they’re damaging the team, according to Burris. Say your employee’s insecurity manifests itself in his getting defensive when interacting with colleagues. “Then you might say, ‘During meetings, you tend to become argumentative and shut down others’ opinions. As a result, we don’t hear what they have to say, which affects our decision-making.” It’s also important to address the impact of your employees’ behavior if you believe it could derail their professional trajectory, adds Shapiro. “Talk to employees about how their behavior is interpreted by others,” she says. Being seen as insecure “could be a real career limiter.”

Build trustDeveloping rapport with anxious employees requires patience and effort. “Play the long game,” says Burris. “You need to spend a good amount of time building trust.” Inquire about the person’s hobbies, family, and interests outside of work. Be supportive and upbeat. “Lay the groundwork to show you care about them, and you are on their side,” he says. Developing a positive dynamic within the team will benefit everyone — and especially your less secure reports. Burris recommends heeding advice from Stanford psychologist Carol Dweck by trying to cultivate a growth mindset whereby colleagues are willing to challenge themselves and grow. “Reorient people’s goals in the workplace to be less about how they’re seen and how they perform and more about how much they improve,” he says.

Clarify expectationsOne of the biggest challenges of overseeing an insecure employee is the impact on your ability to manage your team’s workload, says Shapiro. “When someone doesn’t have the confidence to be proactive or to take on what you’re asking them to take on, you can’t just delegate and move on,” she says. A bit of handholding may be necessary. Be prepared to spend “a lot of time” with your employee especially in the initial stages of an assignment. “This person will have a lot of questions that a ‘secure’ employee probably wouldn’t have.” She recommends initially giving your insecure worker “narrow, concrete types of projects” with well-defined deliverables. “Make sure this employee understands the specifications, the resources available, and the timeline of each task,” she adds. Ultimately, though, the goal is for your employee to operate more autonomously, says Burris. “Explain that your expectations going forward are for the employee to work independently and to make some of the decisions on their own.”

Give specific feedbackTo boost the person’s confidence, “create opportunities for success and then give clear feedback on what enabled that success,” says Shapiro. “This is not a person that you can just say, ‘Nice job’ to.” You need to be definitive and explicit. Give your employee “an inventory of what he or she is good at.” She recommends saying something like, “Let me remind you of how well you did the last time you gave a presentation. You handed out summaries of the PowerPoint. You practiced beforehand. And you and I role-played so that you were prepared for any question the client could throw at you.” Your objective, according to Burris, is to “coach your employees on how to leverage their strengths by reminding them of times they excelled and felt competent.” Precise and detailed compliments “when given in an authentic way” can help to “build up” your employee’s self-esteem.

Pair colleagues togetherIt’s often beneficial to pair your insecure employee with a peer who has “complementary skills,” says Shapiro. Partnering colleagues to work on specific projects helps them each “develop new abilities” and learn how best “to support each other.” You might also consider asking your insecure employee to be a “mentor or coach” to another team member. She recommends saying something like, “Phil, you did great work on that presentation last week. Joe is giving a big presentation next week, and I’d like you to help.” She explains, “By asking your subordinate to coach someone else, it reinforces the value they see in themselves.”

Recognize when your efforts aren’t workingManaging a chronically insecure employee is challenging but you must try not to let your frustration show. That’s not helpful to anyone. And yet, at a certain point, if your efforts to improve the situation, aren’t working, you may have to make a tough call on whether you wish to continue to invest in this person, according to Shapiro. “You have to see the benefit; otherwise you need to ask, ‘Is this worth my time?’” Remember, no matter how hard you try to improve matters, your employee’s self-esteem could be a “deeply rooted and ingrained thought pattern.” And, adds Burris, “if you’re not seeing progress, you have to make the decision whether to let this person go” or to assign him to a different job that’s better suited to him.

Principles to Remember

Do:

Boost your employees’ confidence by providing specific feedback on what they’re good at.

Cultivate trust within your team by showing your employees you care about them and are on their side.

Assign your insecure employee to be a mentor or coach to another team member.

Don’t

Jump to conclusions. What you perceive as insecurity could be a personality quirk or cultural difference. Be careful in your interpretation.

Be wishy-washy. Make sure your employee understands the specifications, the resources available, and the timeline of each task.

Be a martyr. If you’re not seeing progress, either let this person go or assign them to a different job.

Case Study #1: Help your employee feel comfortable and emphasize the importance of learningAnand Prakash, a serial entrepreneur, vividly recalls a period earlier in his career when he managed someone who was insecure.

At the time, Anand was helping to build an incubator for Verizon and the employee — we’ll call him Peter — was a front-end Android developer who had been hired as a contract worker. “Peter was very smart, but he didn’t know his potential,” says Anand. “I thought his skills could be better used on the back-end.”

When Anand proposed this, Peter was unsure. Peter didn’t think he was up to the job. “Peter was a computer science engineer who’d been programming for 10 years — the basic founding blocks were there. But this was something new, and he was scared,” says Anand.

Anand didn’t press Peter at first. Rather, he spent time building a relationship with him and developing rapport. Anand wanted Peter to know that he had his back. “As a manager, my first priority is always ‘what is the best thing for this person?’”

As time progressed, Anand decided to bring up the idea once more. “I asked him, ‘Do you like learning new things?’ Most people say ‘yes,’ and Peter did too.”

So Anand gave Peter “a small, very defined, and very specific” back-end project to work on. “I didn’t make a big deal about it,” he says. “I wanted him to feel comfortable and give him a quick win.”

Peter successfully completed the project in a week. So Anand asked if he’d like to try another one and Peter agreed.

The next project “took him a while to complete, but he did it quicker than he did the first time. He was improving.”

The third project didn’t go as planned, though. Peter made an error that interfered with the servers. The team was annoyed. And Peter was discouraged. “I didn’t make too big a deal about it. I said, ‘Everyone makes mistakes. It’s important to learn from them.’”

Over time, Anand gave Peter larger projects with increasing responsibility. Today Peter is a successful backend developer, and Anand is the CEO of GrailAI, which uses artificial intelligence to detect cancer.

Case Study #2: Partner your employee with a colleague and praise her on what she does wellBen Bloch, a Los Angeles-based executive consultant and strategist, says he’s managed a number of employees who were “quiet, uncomfortable, and insecure” over the course of his career. “I view it as my job to get them to be their best.”

Several years ago when Ben worked as the Chief Marketing Officer for Econation — a clean tech company he co-founded, he managed an insecure employee, who we’ll call Angela. Angela was new to the company and had previously worked in a sales and operational role. At Econation, her position entailed more contact with high-profile customers. She was anxious about it, and it showed.

In the beginning, Ben had Angela sit in on his client conversations. Ben was the role model; Angela’s job was to watch and learn. Later, Ben paired Angela with a more senior member to role-play over and over again how the conversations would take place. “Repetition was key,” says Ben. “I told her, ‘If you know your stuff, you’re going to be more confident.’”

Working closely with another colleague helped Angela get better, but she was still nervous. Ben reassured her that she was improving and offered specific feedback on the things she did particularly well based on what he observed. “I also told her that I still get nervous and that it will come with time.”

Eventually Angela got to be very good at her job. “It wasn’t immediate,” recalls Ben. “But I remember the day when I had a realization when Angela was on back-to-back calls with some big clients. I thought, ‘I don’t have to watch her anymore.’ She was able to advance relationships the way a senior person would.”